Water → HCID 13060509, compound

HRID 2296479Notes

Reaction equation

HRID 2296479 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.CO[CH:21]=[C:22]([C:27]([O:29][CH3:30])=[O:28])[C:23]([O:25][CH3:26])=[O:24].O>CN(C)C=O>[C:13]([NH:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:1][CH:21]=[C:22]([C:27]([O:29][CH3:30])=[O:28])[C:23]([O:25][CH3:26])=[O:24])=[N:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1)(=[O:18])[C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 90770Dimethyl methoxymethylenemalonateHCID 13060453HCID 13060453, compound

Product 1

HCID 13060509HCID 13060509, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-amino-7-pivalamidoquinazoline (10.5 g) and dimethyl methoxymethylenepropanedioate (10.9 g) in N,N-dimethylformamide (32 ml) was stirred at 100° C. for 1 hour and 25 minutes. After the reaction mixture was cooled to ambient temperature, water was added. The resulting solid was separated by filtration, washed with water and dried. The crustals were recrystallized from a mixture of ethyl acetate and ethanol to give crystalline dimethyl [[7-pivalamido-4-quinazolinylamino]methylene]propanedioate (13.7 g).

Workup

  1. temperatureAfter the reaction mixture was cooled to ambient temperature
  2. customThe resulting solid was separated by filtration
  3. washwashed with water
  4. customdried
  5. customThe crustals were recrystallized from a mixture of ethyl acetate and ethanol

Sources & evidence

ORD record
ord-a7c29dc3acea481480c8fdd071c70cee
Source dataset
uspto-grants-1984_01
Patent number
US04429126

Reaction notes

Loading…